Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]- → HCID 73990347, compound

A mixture of 3-methoxy-4-(1H-pyrazol-1-yl)benzaldehyde (1.52 g, 7.52 mmol, prepared as described in Reference Example 5), (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide (4.85 g, 11.30 mmol), and TDA-1 (2.40 mL, 7.50 mmol) in dichloromethane (35 mL) and sat. aq. K2CO3 (35 mL) was heated to reflux for 18 h. The layers were separated and the aqueous layer was extracted with dichloromethane (2×20 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried (MgSO4), and concentrated. THF (20 mL) and 10% HCl (20 mL) were added and the mixture was stirred for 1 h at rt. The reaction mixture was cooled to 0° C., made basic with 10% NaOH, and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 2:1 hexane/ethyl acetate) provided 1.47 g (86%) of the title compound as a yellow solid. MS 229 (M+H)+.

1. temperaturewas heated
2. temperatureto reflux for 18 h
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with dichloromethane (2×20 mL)
5. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. additionTHF (20 mL) and 10% HCl (20 mL) were added
9. temperatureThe reaction mixture was cooled to 0° C.
10. extractionextracted with ethyl acetate (3×25 mL)
11. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
12. dry with materialdried (MgSO4)
13. concentrationconcentrated
14. customPurification by chromatography (SiO2, 2:1 hexane/ethyl acetate)

ORD record

ord-76a7e0df9946439b9f183dd894a60dfd

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613747B2